Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate → (+/-)Methyl 4-[5-(2-cyclopentylacetamido)-1-ethyl-2,3-dihydroindol-3-ylmethyl]-3-methoxybenzoate

HRID 275144ノート

反応式

HRID 275144 の反応式
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH3:20])[CH:14]=[C:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd].C(O)=O>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH2:19][CH3:20])[CH2:14][CH:13]3[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

4

反応物 1

HCID 14626833Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate

生成物 1

HCID 14626834(+/-)Methyl 4-[5-(2-cyclopentylacetamido)-1-ethyl-2,3-dihydroindol-3-ylmethyl]-3-methoxybenzoate収率 80%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 284Formic Acid溶媒

反応条件

温度
80 °C

実験手順

Palladium-on-carbon (10% w/w, 0.5 g.) was added to a mixture of methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (0.5 g., prepared as described in Example 80), and formic acid (99%, 20 ml.), under an atmosphere of nitrogen. The mixture was vigorously stirred and heated at 80° C. for one hour. The cooled mixture was filtered through a pad of diatomaceous earth, the filter cake washed with methanol, and the filtrate evaporated. The resulting oil was dissolved in ethyl acetate (30 ml.) washed with water, brine, then dried (MgSO4) and evaporated. The product was purified by flash chromatography on silica gel (4 cm. diameter column), eluting with 2:3 v/v ethyl acetate:hexane, to give the title compound (0.37 g., 80%) as a foam; NMR (250 MHz, DMSO-d6): 1.04(t,3H, --CH2CH3); 1.15(m,2H, cyclopentyl ring); 1.4-1.8(m,6H, cyclopentyl ring); 2.2(m,3H); 2.7(dd,1H); 2.85-3.2(m,5H); 3.45(m,1H); 3.86(s,3H, OCH3); 3.87(s,3H, OCH3); 6.43(d,1H); 7.20 (m,2H); 7.30(d,1H); 7.50(m,2H); 9.47(s,1H, NH).

後処理

  1. filtrationThe cooled mixture was filtered through a pad of diatomaceous earth
  2. washthe filter cake washed with methanol
  3. customthe filtrate evaporated
  4. dissolutionThe resulting oil was dissolved in ethyl acetate (30 ml.)
  5. washwashed with water, brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe product was purified by flash chromatography on silica gel (4 cm. diameter column)
  9. washeluting with 2:3 v/v ethyl acetate

出典と根拠

ORDレコード
ord-ba260941d05447ec8f3738b7f069d3a1
出典データセット
uspto-grants-1995_02
特許番号
US05391758

反応ノート

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